Last Updated on January 10, 2022 by James McAllister

By: James McAllister


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It may not have seemed obvious at first, but entrepreneurship is not always as glamorous as it is made out to be.

It can be painfully challenging. More so than even a terrible job, with a terrible boss, and a terrible work environment.

Entrepreneurship can be cruel and heartless, and cripple even the most confident and ambitious people to a shell of what they once were.

One of the hardest things about it all? How lonely it can seem when you’re in this dark, uncomfortable place.

I know what this is like, because there have been times when I have felt this way myself. I know how it feels when you are no longer enjoying your business. In fact, I think most entrepreneurs – even those that achieve massive levels of success, despise their companies at one point or another.

And you know what? That’s okay.

What’s not okay however, is remaining in a state of misery forever.

You started your company for a reason, and it takes a certain type of person to make that sort of jump.  In this article, I want to give you permission to feel these negative emotions. Then, I want to help you lay out a road map to help you develop the best course of action heading forward.

I’ve Experienced This Firsthand – And It Feels Like You’re Trapped In Hell

I’ve been running companies since I was 14, and I started my first online business.

I’ve had companies that were quick successes, and companies that never seemed to get off the ground. I’ve had successful exits, and I’ve ran a company into the ground.

A few years ago I set out to start a different type of company – a baby product brand, selling physical products for the first time.

I had recently lost a child and felt so strongly that I needed to do something that could help bring families closer together, even if it could only come in the form of a funny piece of baby clothing, or an article that helped parents become just a little bit less stressed out.

I was in so much pain that this sense of purpose meant more to me than anything. It gave me a reason to be alive when I felt in a very dark place emotionally.

When the company first started, I was able to actually feel that the work that I was doing had meaning – I was able to see the results of my work by actually interacting with the people my company was affecting.

It made me happy.

Then the company grew. I no longer had time to talk with people – at least not parents. Instead, that was all replaced with new hires, lawyers, accountants, factory owners, and a million other people that seemed to need my time every week.

At this point, it wouldn’t have really mattered what industry I was in – the type of work that I was doing would likely be largely the same. I realized that this is what it was like to actually run a company – it was my first that involved so many people at once.

To be quite honest, despite the fact that it had been my most profitable company to date, I wanted to shut it down for good.

There were moments I hated it so much that I would quite literally walk away from millions of dollars just to get away from the company more quickly.

That’s pretty stupid, isn’t it? To have been so sick of running my business, that I wanted to close it and walk away? Even if it meant that I would be giving up everything that I worked for?

It took a lot of hard thinking and valuable discussions within my inner circle to realize something important:

It wasn’t the company that was the problem. It was the role I was playing within it – and what I forced myself to give up. By making a few small changes in the way I approached and thought about things, I could rekindle that fire that I had within me when I first started.

This brings me to a few key pieces of advice.

1. Understand That You’re Not Trapped

People look at entrepreneurs as people who are truly ‘free’ – they’re not enslaved to their bosses, something many people legitimately feel in today’s day and age.

Unfortunately, we know that this often isn’t the case, especially in the early stages of our company.

We aren’t a slave to just one person. We may feel that we have a duty to serve many – not only our customers, but also our investors, our employees, our creditors, our families, and just about everybody else that is counting on us.

Even if you wanted to walk away, it may feel like you can’t. It may feel like you’re letting too many people down, that you won’t be able to face those that you disappointed, or that your reputation will be permanently tarnished.

Please understand that this is not the case, and no matter what happens, you can bounce back.

I’d be happy to give you examples of extremely successful people that went bankrupt several times before making their billions, but in times of emotional turmoil these feel-good stories likely won’t help you. Instead, think things through logically. Remember some important facts:

  1. Nothing is permanent – the good nor the bad.
  2. Most businesses fail. You’re expected to lose, you’re not expected to win. Sometimes, failure is not your fault at all. Luck plays more of a role in entrepreneurial success than many people like to admit.
  3. You always have the option to shut down, change direction, or start something new. Whatever is happening right now does not take away from this fact.
  4. People that turn against you because of your decision to try something different, are not people that you want around anyway. Their true colors would have been shown eventually – the earlier you learn who’s truly with you and who isn’t, the better.
  5. You only need to succeed once. If now is not the time, it doesn’t mean that you won’t succeed in the future.

Now look, I’m not suggesting that you should shut down your company, even if you hate being a business owner right now. That is of course, a last resort. What’s imperative however is that you believe in your heart that you are not trapped in this company forever – you have options.

Knowing this will give you the mental freedom and willingness to make important changes. After all, if you’d just shut it down anyway, and you’re able to do so at any moment, why not try some things out that may improve your situation first?

2. Identify What Aspects Are Creating Your Negative Feelings

Hate for your company is not something that magically appears out of thin air. Chances are, there’s not just one thing you dislike either.

Hate and resentment for your business was likely built up due to a bunch of little things, piling up over a long period of time.

After all, if there was one tiny change you could’ve made to avoid it, you likely would have already taken that action.

Chances are, most of your emotional triggers can be avoided if you simply become conscious of them. By knowing exactly what it is that makes you feel upset, angry, fearful or frustrated, you can begin taking steps to minimize their frequency and impact.

I encourage you to quite literally note down every single thing that stirs a negative emotion in you – what exactly that thing was, and why you think that it made you feel the way it did.

You may find that there are patterns that emerge that can point to larger issues.

This may be best illustrated with a few examples from my own brands.

In one example, I would get extremely angry when Amazon did something to one of our products that I felt was unfair or illogical. For example, refusing to remove a product review that was incorrectly rated as 1 star, because the customer thought that 1 star was good and 5 stars was bad. Most people understand the review system, and seeing one of our products rated 1 star would instantly bring down the amount of people that clicked through to our sales page.

It’s fair to say this would frustrate most people. However, I became far more angry than I should.

Here’s the important point. It wasn’t the 1 star review that made me angry, or even Amazon’s unwillingness to remove it. Because I tracked every time that I felt something negative, I quickly realized that the real issue was that I hated the control Amazon had over the company. Over the coming months, I took steps to decrease our reliance on Amazon and focus more on building up our own store, even though it probably made us less money in the short-term.

Amazon’s BS no longer bothers me nearly as much as it used to, and I feel far more secure in the company’s future because of that change.

In another example, I found myself becoming snappy with my employees, and I felt bad about it. Every time I heard footsteps towards my office, I felt irritated. Every encounter felt like bad news, because they were taking attention away from whatever I was working on.

Of course, the employees are completely in the right – I was the one being a terrible leader.

I understand the importance of a good company culture, a healthy work environment and a close connection with my employees. I truly do care a lot about them, and I have always encouraged them to talk with me about anything and everything.

By tracking what was bothering me emotionally, I quickly learned that I felt this resentment because I felt unaccomplished with a few key tasks that needed to be done each day. I was getting them done before, but it took much longer due to the constant distractions from somebody needing help, coming into my office and staying too long, etc.

I fixed this by setting aside a block of time each day where somebody else is in charge of answering questions, and by ensuring more issues are sorted out in each meeting with somebody. Instead of asking questions one-at-a-time, save them and bring them all to me at once sort of deal.

I was a much more pleasant person to be around after that, and it had a positive effect throughout my entire organization.

Identify what your emotional triggers are, and look deeper into the cause and effect of each. Chances are, there are small changes you can make that would have a very large impact when you implement them.

3. Look For Opportunities To Outsource, Even If You Lose Money

The company will not do well if you hate running it.

Unless you’re just starting out, you really shouldn’t be trying to work 18 hours every day unless that’s something you genuinely enjoy doing. Long work hours – especially without any sort of reward for it all, likely do more harm than good over the long-term.

Similarly to auditing your emotional triggers, I implore you to conduct a full audit of the tasks that you do each day. Quite literally, make a spreadsheet of all of them, and include the following things:

  • How often you do each task.
  • Whether or not somebody else can be trained to do it.
  • And finally, how much happiness, excitement, or fulfillment the task brings you.

I guarantee there is something you could either pass onto another employee, or outsource to a virtual assistant.

Ideally, you would spend your time doing things that are high-value, big-picture, and can only be done by you.

“But James, I’m running a small business. I can’t afford to make any additional hires!

If you’re thinking that, you’re wrong. You can’t afford not to hire anybody. If you really hate your company – your emotional state, let alone the time you’re spending doing something that can be easily outsourced, is costing you a lot more than whatever you’d pay that employee.

Heck, a virtual assistant will only run you $2-3 / hr. How much more clear-headed would you be, how much more would you be able to focus on actually growing your company if you were able to focus all of your time on the things that mattered most?

If the alternative is emotional implosion and shutting down your operations, why not try it out?

Note: Click here to learn about my course on outsourcing to the Philippines, which I consider to be one of the best kept secrets in business.

4. If All Else Fails, Take A Break

If you’re able to do so and nothing else is working, consider taking a break – even if it’s just for a few days.

As entrepreneurs, we are almost always working. Even if we aren’t at the office, or in front of our computers, our brains are still processing things in the background – coming up with ideas and solutions, thinking things through, worrying about one thing or another. There is no tuning out of it. When it always feels like you’re working, it’s easy to become overwhelmed – even if you were originally very passionate about the job.

If you step back for a moment, you’ll likely see that your company plays a very large role in your life – it’s almost part of your identity. It’s almost crazy to think about.

Take a break for a few days. Imagine that you’re retired and no longer have to work again. Just try it out.

Many entrepreneurs, even if they’ve sold their companies for insane amounts of money, become very depressed afterwards and want to return to work. Even when they were ready to step away and sell it all.

Isn’t that strange?

Take a break and see how you feel.


It was a series of small experiences that caused you to lose excitement and begin to hate your company. It will be small actions that help get you out of it in the coming weeks and months.

Regardless of what happens, as long as you continue showing a willingness to improve – and carry a belief that you can, things will eventually get better. I say those both from my own personal experience, as well as observing the experiences of others.

I’d love to hear more about how you’re feeling right now, and what you believe may be contributing to that – good and bad. I want to know about the times you’ve hated your business the most, and the excitement you had when you first started it.

With a willingness to try, things can become so much better.

I believe in you!

– James McAllister


Review the main points of this article in the SlideShare below. Feel free to embed this on your site, use it in your organization, and share it with others! All I ask is that you give credit! (Download links are available from SlideShare’s website, which you can access by clicking the LinkedIn icon)

About the author 

James McAllister

James is the owner of He started his first blog at the age of 11, and has since gone on to start several successful businesses. In total, these businesses have sold hundreds of thousands of units and have touched millions of lives. Here on, he shares his knowledge that brought him to where he is today. If you want to connect with James, follow him on your favorite social networks!

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  1. James- I can’t tell you how spot on this is. It’s Exactly what I needed to hear. I’ve really been struggling as I’ve been through the ringer and, even though the problems are mind now, I can’t find my passion again. Do you do coaching? Would love to hear more follow up podcasts to this one on the same theme.


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